Help! Which bag looks best on me?

The Sienna looks amazing on you and would be great as a casual everyday bag whereas the Totally would be perfect if you're really needing a good large tote and often carry a lot. I personally don't care for the Speedy though; it just doesn't look like it sits comfortably on the body and some things just can't be forced.
 
I like the Totally MM and Speedy B best on you. I think they look best with the casual, pulled together outfit you're wearing. But they all look good on you...I think you could pull them all off.
 
I absolutely loved the Totally MM on you. Didn't care for the PM, though. However, since I've had a really bad experience with this bag, I must say Speedy B or Siena. I'm a complete Speedy B enthusiast, but if you're too afraid of the vachetta, then go for the Siena, it looks lovely on you. If you think you can handle all the vachetta, though, I think the Speedy B is the way. Just today I was admiring the patina on mine, with all its marks and stains. They all bring me back memories and I TRULY love that.
 
Based on what you already own I might go for the totally good tote for a mom and not like your other bags get the big one! Could fit all your and your girls items for travel!